The 25 Most Absurd Photos Of Eccentric Billionaire Richard Branson

Sir Richard Branson is the quintessential self-made, idealistic, and off-the-wall entrepreneur. He's never stopped doing things differently over his 40-plus-year career, from dropping out of high school to run a magazine to buying his own island in the British Virgin Islands — not to mention starting a commercial airline from scratch and kite-surfing across the English Channel in his 60s.

Today he's worth an estimated $5 billion and is the chairman of the eclectic Virgin Group of businesses, which is most recently expanding into the hotel market.

In his new book "The Virgin Way: Everything I Know About Leadership," Branson writes that his love of a crazy marketing stunt or world record attempt is just an extension of the way he runs his businesses. "The problem is that being told 'You'd have to be pretty crazy to even think about doing that' has to me always been like the proverbial red flag to a bull," he writes.

To celebrate his huge personality — and unparalleled marketing savvy — we've collected some of Branson's most outlandish photo ops.

Branson arrived to his 2007 "Rock the Kasbah" benefit for Morocco atop a horse and in traditional Moroccan garb.

Mario Anzuoni/Reuters

Because he lost a bet with Air Asia CEO Tony Fernandes over which of their Formula One teams would beat the other, Branson agreed to dress in drag.

Paul Kane/Getty

Here he is getting his legs shaved in preparation for his transformation into a stewardess.

Bill Hatto/Reuters

For some payback, Branson dumped a tray of drinks all over Fernandes.

Paul Kane/Getty

Branson likes to describe his sense of humor as "cheeky."

Jeff J Mitchell/Getty

Branson dressed as an astronaut to celebrate the anniversary of Virgin Money, holding a contest to send someone into space on a future Virgin Galactic flight.

Lisa Maree Williams

Branson is never one to turn down an opportunity for posing with a model, like he does here atop the tail of a Virgin Atlantic plane.

Ethan Miller/Getty

For the launch of Virgin America's first flight from LA to Philadelphia in 2012, Branson posed with the cast of hit comedy series "It's Always Sunny In Philadelphia," including Charlie Day's "Greenman" persona.

Michael Buckner/Getty Images

For the 2009 World Economic Forum, the United Nations set up a simulated war zone environment for the world's 1% to experience. Here's Branson getting held hostage.

Denis Balibouse/Reuters

The London native poses on one of the islands that's part of the artificial archipelago known as "The World" off the coast of Dubai.

Chris Jackson/Getty

Branson and his daughter Holly took part in a record-breaking cheer for the 2011 Virgin Money London Marathon.

Oli Scarff/Getty

For a promotional event in Mumbai, Branson rode atop a taxi dressed as a traditional Indian musician.

Danish Siddiqui/Reuters

Branson dressed as a butterfly to run the 2010 Virgin Money London Marathon.

Christopher Lee/Getty

He celebrated the 2007 launch of now-defunct Virgin Media's Channel One in typical fashion.

Rosie Greenway/Getty

Branson arrived to a 2013 Virgin Mobile news conference in a vintage military jeep, his clothes an allusion to Latin American revolutionary Che Guevara.

Gonzalo Fuentes/Reuters

He christened Virgin Galactic ship WhiteKnightTwo with a spray of champagne alongside his mother Eve.

Fred Prouser/Reuters

Branson traveled to Nairobi in 2007, where he was installed as a Maasai elder in a special ceremony.

Thomas Mukoya/Reuters

In this photo, Branson test drives his amphibious vehicle, which he took on a record-breaking trip across the English Channel in 2004.

Stephen Hird/Reuters

For the launch of his iPad-exclusive magazine Project in 2010, he posed in a newspaper suit alongside mannequins outside New York City's flagship Apple Store.

Mike Segar/Reuters

Here's Branson helping a bikini model eat a prawn at a Virgin Atlantic promotion in 2004.

Patrick Riviere/Getty

Branson seems to enjoy speaking in front of a blown-up headshot of himself, as he does here in a 2010 presentation in Indonesia.

Beawiharta/Reuters

Sometimes Branson just likes to show up to a news conference in a risque costume, acting as if nothing were unusual.

Robert Galbraith/Getty

Branson hires people who share his enthusiasm for media pranks, as shown by the time he silenced Virgin Blue (now Virgin Australia) CEO Brett Godfrey at a news conference in 2008.

Hector Mata/Reuters

Branson promoted the launch of Virgin Mobile in France by rappelling down the Virgin Megastore building in Paris in 2006.

Benoit Tessier/Reuters

While kite surfing in 2009, Branson said he was stopped by a photographer who asked him to pose with his girlfriend. Of course he obliged, and the resulting photo shoot quickly went viral.